2928. Desonide
Nomenclature
CAS number: 638-94-8
(11β,16α)-11,21-Dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; 11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic
16,17-acetal with acetone; 16α-hydroxyprednisolone-16α,17-acetonide; 11β,21-dihydroxy-16α,17-isopropylidenedioxy-1,4-pregnadiene-3,20-dione; 16α-hydroxy-Δ1-hydrocortisone-16α,17α-acetonide; 16α,17α-isopropylidenedioxyprednisolone; prednacinolone; D-2083; Locapred (Fabre); Locatop (Fabre); Sterax (Alcon); Steroderm (De Angeli); Topifug (Wolff); Tridesilon (Miles). C24H32O6; mol wt 416.51.
C 69.21%, H 7.74%, O 23.05%.
Description and references
Prepn and activity: Bernstein et al., J. Am. Chem. Soc. 81, 4573 (1959); Bernstein, Allen, US 2990401 (1961 to Am. Cyanamid); Lee et al. and Diassi, Principe, US 3536586 and US 3549498 (both 1970 to Squibb). Pharmacological and toxicological studies: Mascitelli-Coriandoli, Fraia, Arzneim.-Forsch. 20, 111 (1970); Phillips et al., Toxicol. Appl. Pharmacol. 20, 522 (1971). Structure-activity studies: Ringler et al., Proc. Soc. Exp. Biol. Med. 107, 451 (1961). Chemical and physical properties: Mantica et al., Arzneim.-Forsch. 20, 109 (1970).
Properties
Small plates or white to off-white odorless powder, mp 274-275° from methanol (Mantica); also reported as mp 263-266° from ethyl acetate-petr ether (Bernstein). [α]D25 +123° (c = 0.5 in DMF). uv max: 242 nm (E1%1cm 356). LD50 in rats (mg/kg): 93 s.c. (Phillips).Therapeutic Category
Anti-inflammatory.
Keywords
Glucocorticoid